Audio tours provide users with individual, more detailed experiences of their surroundings. Some audio tours include a playing device that plays specific audio to a user and headphones that output the audio to that user only. For example, when used on a walking or riding tour of a city street, an audio tour may include various segments corresponding to specific items of interest on and around the street. In conventional audio tours, each of the various segments may be triggered by an active user action, i.e., a button press signifying that the user is at a place corresponding to a segment. The playing device may retrieve the audio locally or over a radio antenna or via a remote server.